luxury houses with pool for rent Suffolk County, United States (page 3)

Savor every ray of sunshine at this elegant and sprawling Amagansett stunner! Perched on top of a rise overlooking a 17-acre preserve, with second story views of the ocean, this gated five-bedroom home is built on a grand scale with abundant room for extended family or friends. An oversized heated pool and plenty of entertaining and lounging space both indoors and out make this an ideal perch from which to enjoy spectacular sunsets and the shops, farm stands, restaurants, and beaches of Amagansett, all literally two minutes away by car. [[Rental Registration # 26-263]] EH RR #: 26-263 Rental Terms: Two Weeks: $75,000

Rental Reg #: 22-1105, Expires 06/29/2024. Chic modern 4 bedroom, 4 bath plus den/office on beautiful 2.4+/- acres located at the edge of East Hampton Village. Enter the double height living room with walls of glass overlooking the patio and child-secure heated gunite pool and spa. The living room kitchen-dining area, principal bedroom and one guest room open to the patio. A fourth bedroom not shown can be set up as guest bedroom. The den/office is set aside for privacy at the front corner of the house. The rolling and expansive lawns are bordered by mature trees and plantings for exceptional privacy. EH RR #: 22-1105 Rental Terms: Other / Short Term - 7/17/23-7/31/23: $36,000

Discover a newly completed 2025 modern residence, quietly set far back from the road for exceptional privacy. Thoughtfully designed, the home features three generously scaled primary suites and a striking great room with balcony, oriented toward serene views of the 100-foot pool, spa, and brick-lined terrace. A covered porch and outdoor dining area invite relaxed gatherings framed by the natural landscape. Inside, a spacious chef's kitchen anchors the main level with Thermador appliances, complemented by a large living room, ensuite guest bedroom. Every space has been crafted for comfort, flow, and effortless living, ensuring an elevated experience throughout your stay. Sustainable features include a greenhouse, garage with electric vehicle charging, and geothermal and solar energy systems. Perfectly positioned for quick access to Bridgehampton's ocean beaches and Sag Harbor's boutiques and restaurants, this modern retreat offers the best of the Hamptons in one tranquil setting. Please call with questions or to make an appointment to view this great property! [[Rental Registration # Pending]] Rental Terms: August - Labor Day: $135,000 Two Weeks: $70,000 August: $110,000 Other / Short Term - 8/1/2026 - 9/30/2026: $165,000 September: $65,000

Also Available: Two Weeks between Aug 1 - Aug 31 28K This very private and dreamy Alfred Scheffer restored home and cottage circa 1967 is surrounded by reserve and views of Accabonac Harbor. Exposed wood beams and an expansive back yard create an atmosphere and environment that set the tone of this great scenic property. It is living with nature at its best. The Barn inspired main house is sited to take advantage of the forever field views and is filled with light. There is a 1st floor ensuite primary bedroom, a kitchen meant for cooking and a barn chic great room. What's special about the living arrangement is the guest cottage creating a true compound and privacy with 2 bedrooms and 2 full baths in addition to a high ceiling studio or gathering spot. The outdoor spaces on 2 acres include a pool, fire pit area, sweeping pastoral vistas and a lovely patio for entertaining off the main house. EH RR #: 25-34 Rental Terms: August: $50,000 Two Weeks: $28,000 August - Labor Day: $55,000

Experience the private island ambience from this three story modern design by renowned architectural award recipient. Perfectly sited for panoramic waterfront views and stunning direct sunsets, it has a private path for spontaneous access to a secluded meandering beach. The open interior hold five bedrooms including two primary suites, seven bathrooms, a waterside enclosed porch, media room, gym, sauna, cold plunge ice bath and massage room. Walls of glass exhibit continuous water views throughout while inviting in soothing coastal air. The water view salt water pool has multiple surrounding decks, covered porches and pool house with bath. Various additional gathering areas include a fire pit with seating quietly nestled in a dune by the Bay. A private marina, waterfront restaurants and the charm of East Hampton Village are moments away. A magical setting, this is waterfront living at its finest. [[Rental Registration # 24-1446]] EH RR #: 24-1446 Rental Terms: Other / Short Term - Short-Term: $125,000 November: $50,000 September: $60,000 October: $50,000

Stylish contemporary featuring 3 bedrooms and 2 baths, lovely grounds and heated pool. Located in East Hampton's Clearwater Beach community. Living room is open with double height ceilings and fireplace. Dining is open also. Hardwood floors, plenty of light.Perfect summer living. [[Rental Registration # 24-1402]] EH RR #: 24-1402 Rental Terms: Memorial Day - Labor Day: $55,000 August - Labor Day: $25,000 June: $10,000 July: $20,000 July - Labor Day: $45,000

Set deep within a private, wooded enclave of Amagansett, 41 Deep Wood Lane offers a rare opportunity to experience one of the East End's most cherished natural settings with remarkable tranquility. Approached by a long, secluded drive and enveloped by mature trees and lush plantings, the property feels deeply peaceful, yet remains moments from Amagansett's beloved farm stands and its world-class ocean and bay beaches-pristine, sought-after stretches of shoreline that define the area's enduring allure. Inside, the home carries an atmosphere of relaxed refinement. Sunlight pours through magnificent windows, illuminating interiors layered with soft tones and natural textures. The aesthetic is collected and organic, inviting, unforced, and quietly elegant. Multiple living spaces offer room to gather or retreat, each shaped by the surrounding landscape. The home features six generously sized bedrooms and five-and-a-half bathrooms, including a main primary suite privately positioned upstairs, a serene sanctuary among the treetops, and a second primary suite on the main level offering its own sense of ease and comfort. A dedicated gym, indoor sauna, and a second prep kitchen on the lower level further enhance the home's thoughtful, restorative nature. Outdoors, the property unfolds into a series of beautifully considered spaces, each deserving its own attention. A stunning gunite, pool with a bluestone surround anchors the grounds, framed by generous seating and lounging areas that invite long, unhurried afternoons. A separate firepit area, complete with its own seating, creates a natural gathering place as the day softens into evening. A large, private outdoor shower offers a refreshing post-beach ritual, while a wisteria-draped pergola provides a shaded, romantic setting for outdoor dining. An outdoor grilling area completes the experience. Everywhere, mature trees and dense greenery create a sense of privacy and immersion in nature. This is a home that feels deeply connected to its surroundings-soulful, secluded, and effortlessly livable. A true Amagansett retreat for those who value quiet luxury, natural beauty, and proximity to some of the most pristine beaches on the East End. [[Rental Registration # RR-26-242]] EH RR #: RR-26-242 Rental Terms: August - Labor Day: $120,000 August: $110,000

Beautifully built, fresh, sunny and spacious, this shingled traditional is sited on 1 1/2 acres of mature trees and grounds. There is a gracious living with a fireplace and double height ceilings, a library with a fireplace, formal dining area, a professionally equipped kitchen with pantry, and 5 bedrooms with 4.5 baths including a oversized master with a study. This is a very comfortable country retreat includes a heated gunite pool. [[Rental Registration # RP170055]] EH RR #: RP170055 Rental Terms: June/July: $120,000 August - Labor Day: $100,000 Memorial Day - Labor Day: $220,000 June: $50,000 July: $100,000 September: $60,000 October: $60,000 July - Labor Day: $190,000 November: $60,000

Lovely cape located on a quiet street, convenient to all the wonderful things East Hampton village has to offer. Tastefully decorated living room and formal dining room, fully equipped kitchen with adjacent breakfast area, 4 bedrooms and 2.5 baths. The property offers plenty of room for fun and entertaining. Rental Terms: September: $25,000 June: $35,000

Enjoy August in this sweet, cozy, updated home with pool. Chef's kitchen, open floorplan with 3 bedrooms, and 2 baths, this home is close to bay beaches. [[Rental Registration # 26-1149]] EH RR #: 26-1149 Rental Terms: Two Weeks: $10,000

Located on an iconic East Hampton Village lane is this incredible home with 5 en-suite bedrooms, plus 2 half baths. Luxe beach vibe decor surrounds you in comfort and style. Open concept living with first floor living room, dining area, centralized cook's kitchen and an oversized den that leads outdoors to secluded grounds with a heated, gunite pool, large patio and an outdoor shower. Upstairs find a spacious primary bedroom with sitting area and a fireplace plus 3 additional en-suite bedrooms. Want more? Head down to the finished lower level for media, recreation, Peloton, free weights, powder room and another en-suite bedroom. This home has all you could want or need for a perfect summer experience! Rental Terms: Memorial Day - Labor Day: $250,000 June: $55,000 August - Labor Day: $110,000 July: $100,000 July - Labor Day: $200,000 Other / Short Term - Year Round: $300,000

Sensational, grand and elegant 5,000 sq. ft. shingled home. Open concept living/ dining/ kitchen, with soaring ceilings, works well for entertaining. There are two first floor guest bedrooms which share a full bath, and beautiful den/office with its own full bath. Second floor has three bedrooms, two of which are primary bedrooms ensuite. There is a full unfinished basement, two car garage, heated gunite pool set in expansive lawn surrounded by exquisite landscaping. Secluded area only 5 minutes to East Hampton Village and close to Sag Harbor as well. Owner is open to other periods. [[Rental Registration # 25-132]] EH RR #: 25-132 Rental Terms: Two Weeks: $30,000 July - Labor Day: $160,000 Memorial Day - Labor Day: $200,000

Also available August for $150K. Turn South from fabled Parsonage Lane onto a long private driveway that leads to this 1.7 acre property that backs onto 16 acres of agricultural reserve. There are 5 bedrooms and 6.5 baths in this immaculate modern design with plenty of South and West facing patio for outdoor dining and taking in the view of the lawns, gunite pool and pool patio. Just minutes to Town Line ocean beach. Rental Terms: July: $110,000 August - Labor Day: $150,000 July - Labor Day: $250,000 Other / Short Term - August: $125,000

Nestled within the coveted Georgica Estates enclave of East Hampton and just moments from the iconic sands of Georgica Beach, this five-bedroom, four-bath residence offers an opportunity to experience one of the Hamptons' most treasured settings with remarkable ease. One of East Hampton's original homes, it carries a sense of history and authenticity that feels increasingly rare. Privately positioned among extraordinary neighboring estates, the property is embraced by mature trees, sweeping lawns, and established gardens, creating a tranquil sanctuary in a premier location. The proximity to Georgica Beach allows for effortless daily rituals - early morning shoreline strolls as the light rises over the Atlantic, spontaneous afternoons by the water, and golden sunset returns as the sky softens into evening. The rhythm of the ocean becomes part of everyday life. Inside, the atmosphere is relaxed and quietly elegant. Sunlight fills the interiors, doors open naturally to the outdoors, and coastal breezes drift through the rooms. The aesthetic is collected and organic - inviting, personal, and uncontrived - offering a refreshing sense of ease. This is a home where sandy towels are draped casually, a place to gather, to read late into the afternoon, and to return from the beach with sandy feet and salt in the air. Lovingly maintained and artist-owned, the home carries a soulful presence. Its aesthetic reflects a collected, organic sensibility - layered, personal, and inviting - offering a refreshing alternative to more polished environments. It is a place to exhale, to gather, to read late into the afternoon, and to return from the beach with sandy feet and salt in the air. A true Georgica retreat for those who value privacy, proximity to the ocean, and the quiet luxury of simplicity. Available August through September. Rental Terms: August - Labor Day: $80,000 July: $75,000

Also Available: June '24 $30k, New Waterfront Modern Barn style home with incredible western facing sunset views across Fort Pond. Offering open floor plan with expansive living room, dining area, and top of the line chef's kitchen with Gaggenau appliances, all with dramatic water views. French doors off the living room open to the patio with retractable awning and infinity edge heated gunite pool. Steps lead down to small dock with easy access to launch a kayak or stand up paddle board for a pond cruise. Rental amenities include sauna, cold plunge, outdoor BBQ, luxury massage chair, LED large screen TV's. Convenient location provides easy access to the beaches, village, and docks. [[Rental Registration # Pending]] Rental Terms: August - Labor Day: $90,750 September: $15,000 June: $33,000 February: $10,000 Memorial Day - Labor Day: $181,500 April: $10,000 Other / Short Term - Year Round: $220,000 March: $10,000 June/July: $90,750 October: $15,000 July: $79,750 January: $10,000 November: $10,000

Now available for a few 2 week periods! This spacious and pristine traditional home boasts over 3900+/- square feet of living space that includes 4 bedrooms, 4.5 bathrooms, formal dining room, an intimate study with large flat screen TV, and an impressive, light-filled two-story great room with fireplace and glass doors that open to the deck. The first floor primary suite with fireplace also opens to the deck area. There's a large, open kitchen with countertop seating and a window lined breakfast room. Everything you need for that perfect entertaining. There's also a first floor living space with an office/ den, and additional ensuite bedroom. Upstairs on the second level you'll find 3 guest rooms and a comfortable media room. The half-acre property has been beautifully landscaped with seclusion in mind and boasts a heated pool, a new, spacious mahogany deck with outdoor shower and new hot tub. A convenient location not far from East Hampton Village and ocean beaches complete the picture. A summer home to enjoy! [[Rental Registration # 24-1422]] EH RR #: 24-1422 Rental Terms: June: $35,000

Situated in a prime south of the highway location in the Amagansett Lanes, this brand new construction house completed in 2019, has 6 bedrooms and 7 baths. Designed by a renowned architect, this 5,500 Sf +/- house has unique sleek modern lines throughout the house. All Four bedrooms on the top floor have ensuite bathrooms with beautiful finishes and custom cement tile floors with radiant heat. There are two additional bedrooms on the main floor in a separate private wing of the house. Multiple living areas offer a seamless blend of privacy and open, light-filled social spaces for family and friends. Large chef's kitchen flows into dining area and the great room with double height ceilings, while the extensive limestone patios surrounding the main residence and the pool house are providing beautiful views of the pool and secluded yard. Finished lower level includes media room, with a wet bar, living area, a ping pong table and a full bathroom. The outside living spaces, provide a one-of-kind experience. The modern outdoor living room area features indoor/outdoor living spaces, dining room, pool house with outdoor living area, all overlooking professionally landscaped grounds, and a saltwater gunite pool. Tastefully appointed with top of the line finishes and understated designer furnishings, the outdoor spaces effortlessly host casual afternoons by the pool. This prime south of the highway location in the Amagansett Lanes and steps to the ocean, offers a luxurious retreat environment with modern interiors and beautifully crafted outdoor living and recreational spaces. Top of the line finishes in and out, this home provides a truly unparalleled experience in this south of the highway location, within walking distance to ocean beaches, Amagansett's restaurants and shops. [[Rental Registration # Pending]] Rental Terms: September: $120,000

Jeremiah Baker built this house in the 1850s from proceeds gained during the California Gold Rush. He later became an entrepreneur operating the first daily stage coach mail from Sag Harbor to East Hampton. Today the house has been renovated to its original splendor, rightfully reclaiming its position as one of the first and most prominent houses in the history-rich hamlet of Amagansett. Combining historical detail and provenance while maintaining right-sized proportions of house, rooms and garden, this property features modern high end appliances and bathrooms ranges from SubZero, LeFroyBrooks, Jura, Waterworks, Steamster, and Wolf. A heated gunite pool, 4 bedrooms and 3.5 bathrooms allow for an immersion into history without sacrificing comfort and convenience. Walking distance to Atlantic and Indian Wells beaches as well as all village restaurants allow for ease of access without planning. This historic house covering 170 years of Atlantic ocean living embraced by mature trees on 0.83 acres offers sunshine and shade, serenity during lazy afternoons of the East End summer, and the perfect venue for wonderful meals in a surrounding that focuses on the irreducible human values of rich conversation and measured elegant timeless aesthetic. [[Rental Registration # 25-824]] EH RR #: 25-824 Rental Terms: September: $40,000

Welcome to 54 Bay View Drive East, Sag Harbor, where modern luxury meets waterfront living. This stunning, award-winning modern estate is a boater's paradise, boasting a deep water dock and breathtaking sunset views over Sag Harbor Cove. With 4 bedrooms, 4.5 modern baths, and 3100 square feet of sleek living space, this home offers the epitome of waterfront elegance. A primary suite on the first floor and an additional secondary primary bedroom suite on the second floor with endless water views complement this unique offering. Enjoy the convenience of a water view Chef's kitchen, multi-level decks, and a heated Gunite infinity pool. The property features geothermal heating and cooling, ensuring comfort with minimal environmental impact. Custom fixtures from Italy and an outdoor wood-burning pizza oven add distinctive charm. Located near Sag Harbor's amenities, a 10 min walk to Long Beach, and the Shelter Island Ferry, this home offers a unique summer retreat. Don't miss the opportunity to experience waterfront luxury at its finest. [[Rental Registration # 251021]] EH RR #: 251021 Rental Terms: August: $185,000 August - Labor Day: $225,000

Escape to the heart of the North Fork in this beautiful, spacious four-bedroom home, perfectly designed for entertaining and hosting. Inside, you'll find ample living space complemented by a fully finished basement—ideal for extra lounging or movie nights—while the private backyard oasis features a sparkling heated pool for endless summer fun. Centrally located just one mile from Breakwater Beach, this home offers unbeatable access to the very best of the region, putting you just minutes away from the charming shops on Love Lane, premier local vineyards, and acclaimed farm-to-table restaurants. Book your stay today and secure the perfect central base for your ultimate retreat!

Offered Sept $8,000. Enjoy the ease of summer on the North Fork in this classic 1910 hilltop home overlooking Orient Bay and Long Island Sound. A three-sided wraparound porch extends the main living spaces outdoors through multiple glass doors, creating a seamless indoor-outdoor flow filled with light and salt breezes. Inside, the home offers inviting spaces for gathering, including a spacious living room with a wood-burning fireplace, a formal dining room, and a generous eat-in kitchen with a butler’s pantry. A TV room/bedroom and full bath complete the ground floor. Upstairs are five bedrooms, including a primary bedroom with a private balcony and half bath, along with a full bath for the four additional bedrooms. The private grounds include an in-ground pool. Latham’s Farm Stand and Orient Village are just a short walk away. September is an ideal time to enjoy this peaceful, timeless retreat.

2026 Rates: NO AVAILABILITY New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio. The interior is open and airy with Chef's Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal dining room. All four bedrooms are located on the second level: 1 Primary En-suite, 1 Junior Suite, 2 Guest Bedrooms and Full Hallway Bathroom. You will enjoy being within close proximity to Goose Creek, South Harbor Park Beach and Southold's vibrant business district!

2026 Rates: April $7,500; May $12K; June $15K; July $25K; A1-LD $27,500; Sept $12,500; October $10K: This beautifully curated home away from home, blends modern design with warmth and style. Experience elegant comfort in your private retreat with natural light, modern decor and thoughtful touches throughout. Nestled on a quiet, tree lined street, this special haven features a front porch, fully equipped open kitchen, and spacious backyard with a pool and fire pit. Enjoy all season living in this home away from home just a 10 minute walk to The LIRR station, Hampton Jitney, and The North Ferry.

OFF-SEASON RENTAL | October 15, 2026 - May 15, 2027 Discover the tranquility of Westhampton’s off-season in this exceptional 2020-built contemporary residence at 50 No. Quarter. This immaculate 5-bedroom, 4.5-bath home offers the perfect blend of modern luxury and Hampton sophistication. The heart of the home features a stunning open-concept layout where a gourmet kitchen flows seamlessly into elegant dining and living areas—ideal for both entertaining and everyday living. Ascend to the third floor to find three beautifully appointed en-suite bedrooms, each boasting generous walk-in closets and private bathrooms. The fully finished basement provides versatile additional living space to suit your lifestyle needs. Step outside to your private oasis featuring a heated in-ground saltwater pool, offering a touch of luxury even during cooler months. This pristine property presents a rare opportunity to experience Westhampton’s serene off-season while enjoying all the amenities of a premier Hamptons residence. Available exclusively October 15, 2026 through May 15, 2027

Northport | WATERFRONT. Gated and enchanting waterfront retreat unlike no other. Fully FURNISHED & renovated Mediterranean inspired home nestled in the heart of Long Islands famed North Shore. Panoramic water views of the Long Island Sound & Connecticut. Foyer w/ sitting area and access to private deck. Open floor plan w/ views from every room. Large scale living/dining room combination. Upgraded EIK with stainless steel appliances. First floor w/ two en suite bedrooms and half bath. Lower level features large scale primary suite with renovated bathroom & steam shower. Additional en suite bedroom w/renovated bathroom. Lower level laundry w/ exterior access. The property features lush landscaping, in-ground pool and and covered cabana/ summer wet bar. Private Beach Access (HOA).